(N6-Benzoyl)-5'-O-[(N,N-diisopropylamino)-(2-cyanoethoxy)phosphinyl]-3'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine

Base Information

• Chemical Name: (N6-Benzoyl)-5'-O-[(N,N-diisopropylamino)-(2-cyanoethoxy)phosphinyl]-3'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine
• CAS No.: 140712-82-9
• Molecular Formula: C₄₇H₅₂N₇O₇P
• Molecular Weight: 857.946
• European Community (EC) Number: 689-911-8
• DSSTox Substance ID: DTXSID301103335
• Nikkaji Number: J1.176.332D
• Mol file: 140712-82-9.mol

Synonyms:140712-82-9;(N6-BENZOYL)-5'-O-[(N,N-DIISOPROPYLAMINO)-(2-CYANOETHOXY)PHOSPHINYL]-3'-O-(4,4'-DIMETHOXYTRITYL)-2'-DEOXYADENOSINE;Adenosine, N-benzoyl-3'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-, 5'-[2-cyanoethyl N,N-bis(1-methylethyl)phosphoramidite];((2R,3S,5R)-5-(6-Benzamido-9H-purin-9-yl)-3-(bis(4-methoxyphenyl)(phenyl)methoxy)tetrahydrofuran-2-yl)methyl (2-cyanoethyl) diisopropylphosphoramidite;N-[9-[(2R,4S,5R)-4-[bis(4-methoxyphenyl)-phenylmethoxy]-5-[[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxymethyl]oxolan-2-yl]purin-6-yl]benzamide;SCHEMBL7206380;DTXSID301103335;N-[9-[(2R,4S,5R)-4-[bis(4-methoxyphenyl)-phenyl-methoxy]-5-[[2-cyanoethoxy-(diisopropylamino)phosphanyl]oxymethyl]tetrahydrofuran-2-yl]purin-6-yl]benzamide;AKOS030589608;F90370;(N6-BENZOYL)-5/'-O-[(N,N-DIISOPROPYLAMINO)-(2-CYANOETHOXY)PHOSPHINYL]-3/'-O-(4,4/'-DIMETHOXYTRITYL)-;Adenosine, N-benzoyl-3a(2)-O-[bis(4-methoxyphenyl)phenylmethyl]-2a(2)-deoxy-, 5a(2)-[2-cyanoethyl N,N-bis(1-methylethyl)phosphoramidite]

Chemical Property of (N6-Benzoyl)-5'-O-[(N,N-diisopropylamino)-(2-cyanoethoxy)phosphinyl]-3'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine

Chemical Property:

• PSA: 168.70000
• LogP: 9.12618
• XLogP3: 6.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 19
• Exact Mass: 857.36658402
• Heavy Atom Count: 62
• Complexity: 1380

Purity/Quality:

97% ^*data from raw suppliers

(N6-Benzoyl)-5''-O-[(N,N-diisopropylamino)-(2-cyanoethoxy)phosphinyl]-3''-O-(4,4''-dimethoxytrityl)-2''-deoxyadenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)N(C(C)C)P(OCCC#N)OCC1C(CC(O1)N2C=NC3=C(N=CN=C32)NC(=O)C4=CC=CC=C4)OC(C5=CC=CC=C5)(C6=CC=C(C=C6)OC)C7=CC=C(C=C7)OC
• Isomeric SMILES: CC(C)N(C(C)C)P(OCCC#N)OC[C@@H]1[C@H](C[C@@H](O1)N2C=NC3=C(N=CN=C32)NC(=O)C4=CC=CC=C4)OC(C5=CC=CC=C5)(C6=CC=C(C=C6)OC)C7=CC=C(C=C7)OC

Technology Process of (N6-Benzoyl)-5'-O-[(N,N-diisopropylamino)-(2-cyanoethoxy)phosphinyl]-3'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine

There total 7 articles about (N6-Benzoyl)-5'-O-[(N,N-diisopropylamino)-(2-cyanoethoxy)phosphinyl]-3'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → α-<(N6-Benzoyl)-5'-O-<(N,N-diisopropylamino)(2-cyanoethoxy)phosphinyl>-3'-O-(di-p-methoxytrityl)-2'-deoxyadenosine (140712-82-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / pyridine / 12 h / Ambient temperature

2: 92 percent / n-Bu₄NF / tetrahydrofuran / 2 h / 22 °C

3: N,N-diisopropylammonium tetrazolide / CH₂Cl₂ / 3 h / Ambient temperature

With pyridine; N,N-diisopropylamine tetrazolide; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00111a009

Reference yield:

N6-benzoyl-2'-deoxyadenosine (4546-72-9) → α-<(N6-Benzoyl)-5'-O-<(N,N-diisopropylamino)(2-cyanoethoxy)phosphinyl>-3'-O-(di-p-methoxytrityl)-2'-deoxyadenosine (140712-82-9)

Guidance literature:

Multi-step reaction with 6 steps

1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 1.) 22 deg C, 1 h, 2.) r.t., 87 h

2: NaHCO₃ / methanol

3: imidazole / dimethylformamide

4: 94 percent / pyridine / 12 h / Ambient temperature

5: 92 percent / n-Bu₄NF / tetrahydrofuran / 2 h / 22 °C

6: N,N-diisopropylammonium tetrazolide / CH₂Cl₂ / 3 h / Ambient temperature

With pyridine; 1H-imidazole; N,O-bis-(trimethylsilyl)-acetamide; N,N-diisopropylamine tetrazolide; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00111a009

Reference yield:

N-[9-((4S,5R)-4-Trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide → α-<(N6-Benzoyl)-5'-O-<(N,N-diisopropylamino)(2-cyanoethoxy)phosphinyl>-3'-O-(di-p-methoxytrityl)-2'-deoxyadenosine (140712-82-9)

Guidance literature:

Multi-step reaction with 5 steps

1: NaHCO₃ / methanol

2: imidazole / dimethylformamide

3: 94 percent / pyridine / 12 h / Ambient temperature

4: 92 percent / n-Bu₄NF / tetrahydrofuran / 2 h / 22 °C

5: N,N-diisopropylammonium tetrazolide / CH₂Cl₂ / 3 h / Ambient temperature

With pyridine; 1H-imidazole; N,N-diisopropylamine tetrazolide; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00111a009

upstream raw materials:

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite

α-(N⁶-Benzoyl)-3'-O-(di-p-methoxytrityl)-2'-deoxyadenosine

4,4'-dimethoxytrityl chloride

N₆-benzoyl-2'-deoxyadenosine